Ever since the dawn of the Web 2.0 era, founders and investors have been mesmerized by the concept of “going viral” — the tantalizing prospect of sudden riches, hewn seemingly out of thin air.

But how well do these companies ultimately perform? Are the most famous examples of viral growth actually success stories in the end?

In order to find out, I’ve compiled a definitive list of the 20 Most Viral Companies of the last decade to help explore the relationship between viral success and actual value creation. And, yes, I chose the listicle format to maximize irony.

Because the definition of “virality” is a gray one, I will ensure that all entries contain all (or most) of the following characteristics:

A short, distinct, and clear period of time in which the company’s rate of growth accelerated beyond anything they experienced before or after. (Note that this excludes companies like Tumblr and LinkedIn who experienced tremendous sustained growth over many years).

Substantial PR and a perception of being “the next big thing”.

A large influx of venture capital predicated on a massive outcome.

The rankings are subjective, and based upon both the scale of their virality, as well as the impact they had on Silicon Valley (either in their crash or in their endless ascent).

Furthermore, I have broken this list into “winners” and “losers”, because there is a purpose to this exercise. Unlike most listicles, this piece aims to illustrate a point: Maybe “viral” is actually a bad thing.

Here we go:

#20 — Chatroulette

By the time Chatroulette exploded, it was already a tale of “what could have been.” Launched in late 2009 by a Russian teenager, the site operated out of a Moscow bedroom. Its explosive growth was second only to its remarkable media attention. It also caught the eye of Sean Parker, who was ready to make it his next Facebook, but instead launched his own version in the form of Airtime. But by the time Chatroulette gained a critical mass of users, which took less than 60 days, the word was out… the world’s newest hit website had succumbed to the world’s oldest profession. Or at least the notion that cheap, free, faceless cyber sex could be attained with enough spins of the wheel.

These days, Chatroulette looks a lot like its core users — sad, empty, and in denial that its time has passed. Fortunately, it is the only entry on this list that did not raise meaningful capital. That is why it just sneaks in.

Verdict: Loss Column

#19 — turntable.fm

Turntable.fm is like the guy in jail who puts his head in his hands every night and moans, “I don’t belong in here”… and, in fairness to the product, it really deserved better. Unlike most of the other fast-rise-fast-fall companies on this list, turntable.fm actually built a cool product that a lot of people liked. Which is why the company became the darling of Summer 2011. It even received the ultimate anointment, a big venture round lead by Fred Wilson. So why did the momentum suddenly stop? Nobody knows. It just sort of happened. The site shut down just over two years later. Its lasting legacy may be Fred Wilson’s beautiful reflection about his (few) struggling investments.

Verdict: Loss Column

#18 — GroupMe

Some companies move fast, and some of them move very fast. GroupMe went from launch to acquisition in almost one year flat. How did that happen? The same way all great 2010-era apps succeeded… first it won a major hackathon, then it won SxSW. Throw in a great PR firm and just like that, GroupMe sold for a cool $85 million (though reported numbers have varied). That’s not to say that it wasn’t a terrific app — it certainly was. But GroupMe’s greatest contribution to the startup world was the lesson it taught us: don’t be afraid to sell when a great offer comes along.

Sure, it could have been bigger, and we will never know what the founders might have achieved were it to stay independent. But the app is still very popular today, and everyone made money. It belongs in the “win” column.

Verdict: Win Column

#17 — Ning

“The Social Network to End All Social Networks” had a convincingly simple premise behind it. Who needs Facebook when you can create your own Facebook? And, for a while, it seemed like it was working incredibly well. Ning’s growth was breathtaking, at least in terms of its reported metrics. By late 2008, it was adding millions of users per month, a titanic growth curve that earned it $100 million in venture capital from top names like Marc Andreesen. But the substance wasn’t what the public imagined, and by 2010 the CEO had been replaced. Ning’s incredible PR and huge fundraising were probably instrumental in its initial user surge. And its privately-held data means that we will never know exactly how much was smoke and mirrors. The company quietly exited in a cash-and-stock deal with Glam Media, which appeared to get some of the money back to investors.

Verdict: Loss Column

#16 — OMGPOP

Gaming companies are a “hits driven business,” but in the case of OMGPOP, their story comes down to one massive hit — Draw Something. And what a hit it was. After years of moderate success and careful tinkering, initially as a dating game, the company had a breakout app that went so unbelievably viral in early 2012, that Zynga ponied up nearly $200 million to buy it as fast as humanly possible… which proved to be about thirty days too soon… because the popularity suddenly and unexpectedly dwindled within days of Mark Pincus’s wire hitting the bank. The story did not end well for the then-subsidiary. Zynga basically wrote off the acquisition, laid off a bunch of employees, and then shuttered OMGPOP’s iconic NY office. Founder and CEO Dan Porter — who previously ran Teach for America — made a truckload of money at Pincus’s expense. So who says that nice guys can’t finish first? Too bad OMGPOP’s ultimate legacy was its perfect timing.

Verdict: Loss Column

#15 — BuzzFeed

Sometimes a company has a CEO so good that it can’t help but succeed. One who will literally stop at nothing to create the next big thing. BuzzFeed has that in Jonah Peretti, who previously co-founded a little website called The Huffington Post. After raising a few million dollars in venture funding and perfecting his secret recipe, Jonah unveiled the ubiquitous site we know today. It’s hard to believe that the company’s insane traffic — amongst the top fifteen largest sites on the web — has grown a staggering 400 percent in 2013. Who ever heard of a company going viral after it already has 25 million users? That sort of hockey stick growth is not supposed to happen when you are already gigantic. That is the magic in play here. BuzzFeed still has a lot to prove, and it is still frighteningly dependent on Facebook for its users. But it’s hard to imagine a poor outcome for the country’s best media entrepreneur.

Verdict: Win Column

#14 — Bebo

Sometimes, an acquisition can be so disastrous, that it costs a CEO his job. That is what happened to legendary media executive Randy Falco, who paid $850 million for Bebo, after it had clearly won the bronze medal (at best) in the Social Network Wars. Bebo had used every trick in the book to grow its audience to a whopping 40 million users, and pointed to massive engagement during its year-long negotiation with AOL. How this deal got done after such thorough due diligence is a true mystery.

To credit Bebo founders Michael and Xochi Birch, they really knew how to drive viral growth patterns, and Bebo did manage to gain dominance in Ireland and parts of the UK, before quickly surrendering the crown to Facebook. But it has not stopped Bebo from being considered the frothiest acquisition of the Web 2.0 era. Not that the founders, $595 million richer, cared. They managed their cap table as astutely as their growth strategy, and have a Pacific Heights mega mansion to show for it. And earlier this year, the Birches bought Bebo back for a paltry $1 million.

Verdict: Loss Column

#13 — Fab

2011 was a year that lived up to the company’s namesake for the men at Fab.com. After struggling as an unsuccessful LGBT social network — or a “gay Yelp” as they called it —the company pivoted into a sort of “flash sales with taste” business model, built around co-founder Bradford Shellhammer’s remarkably keen eye for merchandise. The growth was explosive. Within a year, the company had raised a whopping $40 million at a staggering $200 million valuation, and they doubled that four months later.

The monster growth and suddenness of the pivot had turned Fab.com into a Silicon Valley darling, and earned it a coveted billion dollar valuation by this summer, but even its fundraise announcement was tinged with doubts. Those concerns have proven very real, and now Fab.com is embattled with huge layoffs and the eyebrow-raising departure of Shellhammer. It’s COO, who thrived at Etsy, also left. Hope is not lost for the company, but with $300 million in VC and debt already raised, the goalposts are running away from reality. It’s too early to write Fab.com’s eulogy, but they are facing a tremendous uphill battle. With more game plan changes being announced, the company will have to hang out in the “loss” column until it can prove the skeptics wrong.

Verdict: Loss Column

#12 — Second Life (Linden Lab)

I don’t know what to say about Second Life. I’ve never been on it. It scares me. I am not even super comfortable writing about it. But in 2007, Second Life became huge. Massive. It had millions upon millions of users and was going to change our world forever. Its valuation quickly hit $700 million. The website (if we can even call it that) put the concept of “avatars” on the map. It put the concept of virtual goods and virtual currency on the map. It was huge in Europe. Our parents wouldn’t stop asking us about it. Everything changed.

Or it wasn’t, and everything was inflated PR bullshit. Who is to say?

Verdict: Loss Column

#11 — Viddy

Viddy’s sudden rise and fall can be summed up easily in a chart. But its virality is not the fun part of the story. The fun part is when Viddy raised the “party round to end all party rounds.” Top-tier venture funds like NEA and Khosla weren’t enough. The nation’s premier investment bank Goldman Sachs was not enough. International pop superstar Shakira was not enough. So they brought in World Cup soccer hero Gerard Pique of Spain to round out their $30 million Series B. The valuation was rumored at $370 million. All of this took place only three months after raising a Series A at much lower numbers. But the cops (Facebook) busted up the party, just as the crowds arrived.

The company’s placement on this list; however, is enhanced by the responsible and shocking action that took place next… the founders gave the money back. Or at least most of it, according to Crunchbase, which now lists a much smaller round in place of the $30 million. Oh, and the company has pivoted its branding to be called Supernova. Given their reasonable and responsible handling of events, I think that most of us should wish them good luck as the future plays out. But as for Viddy, it will be counted as a loss.

Verdict: Loss Column

#10 — YouTube

YouTube was not the first website where users could upload and host their videos in the cloud. That honor may belong to my cousin Jake who launched Vimeo in 2004. But YouTube had an ace up its sleeve that set it apart from all other video hosting services of the time… a stolen Saturday Night Live music video called "Lazy Sunday." Launched in mid-2005 after receiving funding from Sequoia Capital, YouTube grew at a nice pace until somebody decided to upload (without permission) a hilarious SNL sketch that went viral in its own right. And took the hosting platform to new heights with it. YouTube’s founder denies this version of history, but everything that happened after "Lazy Sunday" was like a dream come true. The growth was mind-numbing. The cultural impact was astounding. The service basically won Time Magazine Person of the Year for 2006. The only reason why the website is not listed higher is because it probably sold for one-tenth of its potential value. And that would have been if they waited just one more year. But a win is a win is a win.

Verdict: Win Column

#9 — Digg

Oh, what could have been, and oh, what has since come to pass… were we to count a site as a winner based simply upon the impact it had on other sites, then Digg would be right up there. Unfortunately, that is not how this works. Before Reddit replaced Pluto as our ninth planet, and before everything had a “Like” button on it, there was Digg. Founder Kevin Rose was on the map before Digg, but it was the website that made him (paper) rich. As Sarah Lacy’s unforgettable cover story on BusinessWeek proudly claimed, “this kid made $60 million in 18 months”. That cover is what made me want to start a company. Everything was a dream come true for my idol Kevin Rose… until the day that Digg refused to stand up to the corporations that wanted to sue it. Users revolted due to perceived ‘selling out’. That, teamed with Facebook’s rise, changing tastes, plus some Founder vs. CEO tension, and a rejected buyout offer… well, it all added up to an unhappy ending.

The good news is that Digg’s demise did not seem to hurt a single person affiliated with the site. Rose made a fortune as an investor, and its backers Reid Hoffman and Marc Andreesen are doing just fine. Digg gets a loss, but its participants are still winners.

Verdict: Loss Column

#8 — Slide and RockYou!

These two were basically the same company, so they both get to be commemorated together as twins. Looking back in time, one can hardly believe that they even existed, but the two Facebook-app workshops deserve to be remembered as the ultimate ‘right place at the right time’ beneficiaries. Backed by the best investors on the planet, and powered by some initially unreal user numbers, the two companies raised a combined $200 million. I will pause for a moment as you put your eyeballs back into their sockets. In a lesson that others would one day learn, Facebook pulled the rug out from under Slide and RockYou! Hamish McKenzie’s outstanding exploration goes into more detail, but the Facebook App ecosystem never achieved what investors hoped it would. And neither Slide nor RockYou! could live up to their massive valuations. The former got a fortuitous buyout from Google, while the other is still independent.

Verdict: Loss Column

#7 — Snapchat

This is the only entry on the list that will not have a verdict, because it is so new. But one cannot discredit the trajectory it is on right now: up, up, and away. The company, whose founding story has Aaron Sorkin licking his chops for a "The Social Network" sequel (with double back-stabbing), is on an absolute tear. It just turned down a $3 billion offer from Facebook, and the CEO has already cashed out big time. Oh, and it doesn’t make any money. Basically, Snapchat is like 2010 all over again. But maybe it will work. Facebook is terrified that it has lost its cool factor with teenagers, and Snapchat has proven that it is about more than sexting. The future looks bright, but it’s still too early to say that it won’t get MySpace-d by Zuck and the gang.

Verdict: TBD

#6 — Glam Media

It may not be as famous as some other companies on this list, but Glam Media boasted some eye-popping growth numbers during its peak. In fact, back in late 2006 and early 2007, its growth rivaled Facebook in the eyes of stunned venture pundits. Glam grew so much in 2007, that it really had nowhere else to go. It hit the ceiling. But, unlike famed rapper Macklemore, the ceiling has proven more than able to hold Glam Media. And, so, for almost three years now, Glam Media has rumored about an upcoming IPO. But it never comes. And since other AdTech companies like Criteo and Rocket Fuel have IPO’d with lukewarm results, this is bad news for the company that has raised a whopping $180 million already. Not to mention the $150 million it spent on Ning. Unlike most viral companies, Glam’s fall has not been sudden. In fact, the company’s value has probably been more of a flatline than a descent. But this is not where they thought they would be at the end of 2007. This company’s high ranking is compounded by the fact that Glam Media represents the entire Ad Network industry, and because it is the third largest web audience on the planet according to Quantcast. When a giant plods around in circles, it is very loud.

Glam’s excellent investors, terrific sales team, and incredibly persistent CEO should ensure a respectable end to this story, but a “big win” is going to prove elusive for all involved. And since this long-rumored IPO is proving less tangible than the golden city of El Dorado, we are going to have to count it as a loss for the time being.

Verdict: Loss Column

#5 — Twitter

More than any site on this list, Twitter’s virality can be associated with a very specific time and place. At the SxSW 2007 conference, Twitter was all the buzz. It had previously been a pet project (and pivot) for well known entrepreneur Ev Williams and his ace product team, who actually created and crafted the idea. It had gained a small amount of traction prior to the Austin festival, but it cemented its status as the app to use when panelists and other influencers wouldn’t stop talking about it. The rest is history.

Verdict: Win Column

#4 — Pinterest

Few companies earned their viral success more so than Pinterest, which initially launched to little fanfare in 2010. But the founders nurtured a small and highly-engaged community of devotees, before releasing outstanding mobile apps to support the product’s true potential. And when it popped, it popped. The site achieved escape velocity in Summer 2011, and it has never looked back. Though still private, the company is almost certain to follow in the footsteps of Facebook, LinkedIn, and Twitter — and its monetization potential could be huge once retail/commerce aspects are figured into the equation.

Many social networks have been built upon spam loopholes, gimmicks, and seedy use cases. That was never the case with Pinterest, who showed up fashionably late to the social network party, and did so with total style. Despite its success, the company’s founders keep a low profile and spend their days building. And if all of this gushing praise sounds a bit far fetched — then, fine, guilty as charged. Because there are few Silicon Valley companies that deserve to get more and more favorable attention than they already do. Pinterest is one of them.

Verdict: Win Column

#3 — MySpace

Should this be higher on the list? Should it be lower on the list? Should it be on the list at all? Those questions pretty much sum it all up with MySpace. It was the social network that won it all. In mid-2005 the company was bought by NewsCorp for “only” $580 million. Then the real virality started, because one year later it was the biggest website on the entire Internet. Bigger than Google. But we all know how the story ends. MySpace was the proverbial “hare” to Facebook’s “tortoise”. It’s mega ascent and apparent victory in a winner-take-all category is the perfect example of virality’s illusion. In fact, if I really wanted to, I could make this paragraph one giant schmorgesborg of ominous and enlightening parables, allusions, fables, and life lessons. But one day a great writer like Ron Chernow or Malcolm Gladwell will do that for me.

Suffice it to say, MySpace made a bigger crater than any viral crash landing before or since. Other than Tom and the guys at Redpoint Ventures, there are few winners in this tale. But, hey, $580 million ain’t bad, so it’s not No. 1.

[Note: As a courtesy to everyone, I will unofficially bundle Friendster in here, too]

Verdict: Loss Column

#2 — Instagram

Oh my god, Instagram. Like, seriously. Holy fucking shit. One minute I am making fun of my hipster friends for futzing around with sepia filters on their obnoxious travel photos… the next minute Kevin Systrom has $1 billion. Oh, and the day before he got the $1 billion, he raised a venture round in the neighborhood of $500 million. An overnight doubling of value? Yeah, that’s virality. Oh, and before that, he hired almost nobody, so he got to keep most of the payload. And before that — shit, seriously — I can’t even with this company. I just can’t. I CANNOT RIGHT NOW. It’s totes a win. Ugh.

Verdict: Win Column

#1 — Groupon

“The Fastest Growing Company of All Time” was a designation that rained down upon Groupon at its peak. Based upon perhaps the simplest and most clever business model in web history, no superlative was spared in describing both the company and the category that it inspired. People estimated that daily deals could be a $100 billion business. And Groupon put up real revenue numbers to boot, a welcome departure for most Silicon Valley high-flyers (even though it was based in Chicago of all places). But this amazing business model from heaven was too good to be true. The economics just didn’t add up for its core customers, as a few lonely, astute observes predicted during its magical 2011 year.

The company ultimately IPO’d after turning down a huge check from Google, but the offering fell flat before most could sell. Its value tanked, and has never come close to its starting price. CEO Andrew Mason was fired. And while its current valuation is still $6 billion, that has to be put in the context of the $1.15 billion it raised in venture capital and the $700 million it generated from IPO proceeds. That, teamed with the dilution caused by innumerable acquisitions, means that many top VC’s have little to show for their investment. If one bundles Groupon’s cousin LivingSocial in this mix, the outcome is even worse for investors. But what’s tragic is that the bulk of losses were endured by everyday people on Main Street. There were some big winners in the Groupon story, but innumerably more losers. It was no Ponzi Scheme, but the outcome sure feels like one sometimes. And, so, at this moment in time, Groupon goes in the “loss column”.

Verdict: Loss Column

Final Score: 6 Wins, 14 Losses

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Epilogue — Facebook

It was a tough decision, but I’ve decided not to include Facebook on this list. An explanation is certainly owed. The question is one of definition — was Facebook truly “viral”? Compared to some on this list, yes, of course it was. That said, it was also the “tortoise” to MySpace’s “hare” and an example of steady growth over many years (albeit on a large scale). Indeed, it’s hard to pick any one year as the “breakout” year for Facebook. As late as 2007, people were writing off the company.

But the reason why I’ve ultimately decided to omit it is simple: At so many moments in its history, Facebook sought to limit and control its own growth. This separates it from all other companies on this list. It first did this upon launch in 2004, when it phased colleges onto the platform at a pace that would be considered glacial by today’s standards. I remember watching as my friends at non-Ivy-esque colleges pouted and waited for the day their school got added. And it wasn’t until well after that high schools got added… then parents… then brands and corporations.

In short, I think that Facebook is in-and-of-itself a testimony against virality. Perhaps it is telling that the most seemingly-viral product of our generation chose to hit the brakes time and time again.